2,5-Dihydroxy-1,4-benzoquinone

2,5-Dihydroxy-1,4-benzoquinone or 2,5-dihydroxy-para-benzoquinone is an organic compound with formula C
6H
4O
4, formally derived from 1,4-benzoquinone by replacing two hydrogen atoms with hydroxyl (OH) groups. It is one of seven dihydroxybenzoquinone isomers. It is a yellow solid[1] with planar molecules[2] that exhibits ferroelectric properties.[3]

2,5-Dihydroxy-1,4-benzoquinone
Skeletal formula of 2,5-dihydroxy-1,4-benzoquinone
Skeletal formula of 2,5-dihydroxy-1,4-benzoquinone
Ball-and-stick model of 2,5-dihydroxy-1,4-benzoquinone
Ball-and-stick model of 2,5-dihydroxy-1,4-benzoquinone
Names
Preferred IUPAC name
2,5-Dihydroxycyclohexa-2,5-diene-1,4-dione
Other names
2,5-Dihydroxy-p-benzoquinone, anilic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.505
UNII
  • InChI=1S/C6H4O4/c7-3-1-4(8)6(10)2-5(3)9/h1-2,7,10H checkY
    Key: QFSYADJLNBHAKO-UHFFFAOYSA-N checkY
  • InChI=1/C6H4O4/c7-3-1-4(8)6(10)2-5(3)9/h1-2,7,10H
    Key: QFSYADJLNBHAKO-UHFFFAOYAW
  • C1=C(C(=O)C=C(C1=O)O)O
  • O=C\1C(\O)=C/C(=O)C(/O)=C/1
Properties
C6H4O4
Molar mass 140.094 g·mol−1
Melting point 212.5 °C (414.5 °F; 485.6 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

The compound is a weak acid: one or both hydroxyls can lose a proton to yield the anions C
6H
3O−
4 (pKa1 = 2.95) and C
6H
2O2−
4 (pKa2 = 4.87), respectively. The latter forms a variety of metal complexes, functioning as a binucleating ligand.[4]

The compound has been identified as partly responsible for the color of aged cellulosic materials.[5]

See also

References
  1. Onkar Singh, Aran Kumar, and Karan Singh (2012), "Polymeric complexes of 2,5-Dihydroxy-1,4-benzoquinone with some Lanthanides". International Journal of Scientific and Research Publications, volume 2, issue 9 ISSN 2250-3153
  2. Semmingsen, Dag "The crystal and molecular structure of 2,5-dihydroxy-1,4-benzoquinone at -162°C" Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry 1977, volume B31, 11-14.
  3. Horiuchi, Sachio; Kumai, Reiji; Tokura, Yoshinori "Hydrogen-bonded donor-acceptor compounds for organic ferroelectric materials" Chemical Communications 2007, 2321-2329. doi:10.1039/B617881B
  4. Kitagawa, Susumu; Kawata, Satoshi "Coordination compounds of 1,4-dihydroxybenzoquinone and its homologues. Structures and properties" Coordination Chemistry Reviews 2002, volume 224, 11-34. doi:10.1016/S0010-8545(01)00369-1
  5. Hosoya, Takashi; French, Alfred D.; Rosenau, Thomas "Chemistry of 2,5-dihydroxy-[1,4]-benzoquinone, a key chromophore in aged cellulosics" Mini-Reviews in Organic Chemistry 2013, volume 10, pp. 309-315.


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